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I think it's fair to say that over the years, singing has eluded me. My first singing instructor said some variant of, "I don't think you're tone deaf, but I'm not positive." to me.
I got into learning how to sing after I began acting. A number of folks would just randomly ask me if I sung and since I said no, they recommended that I start singing. I'm not terribly certain why -- I'm not sure if there's something about my speaking voice that lends itself to singing or not.
While I was living in New York, I studied at two different places. Both, I think, are pretty fine places to study. The instructors are themselves accomplished singers and they both have an impressive roster of professionals (some famous, others are working singers on Broadway, etc.) However, despite what is probably excellent instruction, I couldn't get to where I wanted to get to. This may not sound like a high standard -- but I wanted to be able to sing a song, on my own and without my instructor there to adjust me, with only a musical instrument to key off of. (not necessarily even having the ability to sing a capella.) When I got to Williamstown, they had open tryouts for cabaret and the musical director had us to sing a capella (claiming that he didn't feel like playing the piano.) I thought that was a bit much, but in reality, ability to sing a capella really does separate out the talent very quickly. I was separated out :)
A little discouraged, that incident did re-orient my standard around progress. Before, incremental progress was sufficient, now I basically said, "It's not singing unless I can sing on my own -- just with a piano or guitar." I went back to New York to continue plodding along but ended up moving to L.A. in short order (more on that in another post.) When I got to L.A., I didn't have a singing instructor and singing wasn't a particularly high priority for me as I was trying to sort out my non-existent acting career. Even in New York, I considered it more as a hobby than something I wanted to seriously pursue.
One night at the Magic Castle, I made a couple of new friends -- Holland and her boyfriend, Jason. Holland is a professional singer (recently was part of a group of great singers who did covers of Frank Zappa songs as a tribute.) [link] We got to talking and I mentioned how I didn't have someone to study with out here and she said, "I have just the guy for you." That's how I got introduced to Gerald White [link].
So for the past 4 months or so, I've been going every week and studying with Gerald. Singing is pretty fascinating to me because it's incredibly technical -- way more than I certainly expected. We're running scales and exercises the dominant portion of our lesson (though the amount of time on that has been relatively decreasing.) 
One day, Gerald mentions to me that his studio has regular showcases, they have one coming up, and asks me if I want to take part in it. ?!?!? I thought this was astounding and really hard to believe. My first reaction, believe it or not, was suspicion. I would say my overall level of confidence in terms of where I'm at singing-wise is definitely low. I just feel like I have many miles to go. I also think that's factually true and not just false humility -- I'll explain more about that in a second. I immediately say yes, but after a couple of more weeks -- I express concern because some basic things -- like when to come in for certain verses, timing / rhythm, and to some extent even staying fully on pitch -- I just don't have as firm a grasp as I'd like. Gerald thought this was reasonable and we decide to push to the next showcase.
That brings us to today. For the past several weeks, we've been toying around with a handful of songs. "Half of My Heart" by John Mayer, "Hey, Soul Sister", by Train, and "Learning to Fly", by Tom Petty. Gerald is pretty big on "Learning to Fly" -- he just thinks that's in my wheelhouse, I stay on pitch well -- it's something I can really work with. However, today he wanted to just play around with another song. So we start off with "Hey, Soul Sister" because he noticed that I was doing really well using my falsetto in the warmups. This is a totally bizarre song for me to sing because I'm in falsetto the entire time. I don't even recognize myself and upon hearing the recording of myself -- it's clear that even though I basically stay in pitch, I'm definitely straining many times throughout. It's actually such hard work for me that I can not sing this song in the car (at least not in falsetto; it's ok if I sing an octave down.) The reason is because it takes so much mental energy for me to sing for such an extended period of time in falsetto that I don't feel comfortable driving simultaneously. 
I then tell him, "There's this one song that I sing that I feel really comfortable with -- I usually go to it if I'm having trouble with other songs. It's OMG by Usher." Now, for those of you who know me, this is probably a rather surprising song for me to work -- it's hip hop (though I love hip hop, I don't give off that vibe :) ), it's Usher +, and it's a racy song. But there's something about the range of the song that matches very closely to (I think) my range because I have a lot of freedom when I sing it and feel like I match pitch closely.
I sing first time through off my iPod so then I have Usher's and's voice to key off of (so much easier than just the instrument because there's so much more information -- I also seem to just match human voice more easily). I sing it and he simply goes, "That's much better. Do you feel it?... It's right in the meat of your range."
So that's where I'm at -- it's going to be "OMG" or "Learning to Fly". If it's "OMG", I think that's going to be super strange but hopefully a lot of fun. We'll see, I'm excited about it but also think there are a lot of things I have to improve to get there. Frankly, I need to spend time just to remember all the lyrics, really getting where I'm supposed to come in throughout, let alone like singing singing. But I think the latter that's something that's just going to have to come over the years (hopefully :) )